MILF Paradise System

Chapter 41: MILF on Rooftop Pool


"Hey… what's wrong?" I asked again, softer this time, my hand sliding up to cradle the back of her head.

She was still sobbing, shoulders shaking against my chest, the wet crop vest clinging even more from her tears and the rain mist.

Finally, she pulled back just enough to look up at me, eyes red and glassy. "I… I miss what you have with Lily, Alex."

I stopped, confused. "What do you mean?"

She wiped at her cheeks, voice breaking. "I know what your relationship with Lily is, Alex. I saw you both outside the office room on the ground floor that one time… and I heard everything last night. The walls are thin."

So that's why she crashed last night. Jealousy. Pure, raw envy. She wanted what Lily had—with me.

I searched her face, the sadness still there, mixed with something vulnerable and hungry.

My cock was throbbing now, pressed against her stomach through my jeans, the heat of her body making it impossible to think straight.

"Hey," I said low, pulling her closer again. "I'm here for you, Autumn. Whatever you need."

She clung tighter for a second, then suddenly froze—feeling my hardness against her. Her eyes widened, cheeks flushing deeper as she realized.

"I'm sorry, Alex," she whispered, pulling back fast, hands pushing gently at my chest. "I don't know what came over me. This is… really inappropriate."

She stepped away, arms wrapping around herself, looking embarrassed and small despite the way her soaked clothes hugged every curve.

"It's okay," I said, reaching for her again. "You can let it all go. I don't mind."

"No… Alex, I'll be fine," she murmured, turning toward the rain again, voice shaky.

I sighed, running a hand through my wet hair. Damn. Missed the mark.

"Okay, Autumn," I said finally. "I'll be going then."

I turned to leave, glancing back once—she was still standing there, looking lost in the storm, sad and alone.

I was soaked anyway from the rain and her clinging to me. Might as well check out the rooftop pool on the 10th floor—Lily had mentioned it once, said it was private and awesome. I hadn't been yet.

But as I hit the stairs, I called back over my shoulder, "Autumn—you should enjoy your life. Whatever problem you're facing, it's not bigger than your happiness. Weather's perfect for the rooftop pool. Come join if you feel like it."

I didn't wait for an answer, just headed up the stairs two at a time.

Reached the top, scanned my fingerprint—Lily had added me—and the door clicked open.

The rooftop was open-air, rain pouring down hard, the big pool shimmering under the storm lights, shower rooms off to the side. Empty, private, perfect.

I stripped down to my boxers, tossed my clothes under the covered area, and stepped out into the downpour. Hard rain like needles, cold and sharp against my skin—felt fucking amazing after the day I'd had.

I stood there for a few minutes, head tilted back, letting it wash over me, thunder rumbling low, the storm rinsing everything away.

Then—the door clicked open behind me.

I turned.

Autumn.

She stepped through, still in that tiny white crop vest and cotton panties, now completely soaked from the rain she'd walked through to get here.

The thin fabric clung to her like a second skin—crop top transparent, nipples hard and dark through it, tits heavy and outlined perfectly. The panties were plastered to her, riding low, the wet cotton molded to her pussy lips and disappearing between those plump ass cheeks.

Water streamed down her body, over her flat stomach, dripping from her curves. She looked vulnerable, determined, sexy as hell— skin glistening.

Our eyes locked.

She didn't say anything at first. Just stood there in the downpour, letting it soak her completely, arms wrapped loosely around herself.

I smiled, genuine this time. "I'm glad you came, Autumn."

She tried to smile back—a small, shaky curve of her lips—but it didn't reach her eyes. She still looked gloomy, the sadness lingering like the dark clouds overhead, heavy and unspoken.

The rain pounded between us, waiting.

She stepped fully into the rain, letting the door click shut behind her.

"I thought I'd take your advice, Alex," she said, voice soft but trying for light, tilting her face up to the downpour like she was forcing herself to enjoy it.

Water streamed down her hair, her neck, soaking the thin crop vest even more until it was practically see-through.

Then her gaze dropped—slow, unavoidable—and landed on the front of my boxers.

The bulge was impossible to miss now, thick and straining against the wet fabric, outlined perfectly from everything she'd done to me just by showing up like this.

Her eyes widened for a second, cheeks flushing deeper than the rain could explain. She bit her lip, looking back up at me—half embarrassed, half something else.

I didn't hide it. Just stood there under the pouring sky, letting her see exactly what she did to me.

Then I stepped closer, the rain pounding between us, and reached out my hand. "Come here, Autumn."

She hesitated for a heartbeat, eyes flicking from my face to my outstretched palm, then took it. Her fingers were cold and trembling as I pulled her gently toward me, close enough that the heat of her body cut through the chill of the rain.

"Now tell me what's been eating you," I said, voice low, thumb brushing over her knuckles.

She looked away, rain streaming down her face like tears she wasn't shedding anymore. For a second she couldn't speak, lips pressed tight. Then it spilled out, quiet and broken.

"It's my husband, Alex."

I frowned, water dripping from my hair. "What about him?"

She stepped even closer, her soaked body almost brushing mine, voice barely above the rain. "He left me last month. Said I… wasn't enough for him."

What the fuck.

I stared at her—this sinful, perfect body pressed near me, curves that could ruin a man, skin glistening, tits straining against that soaked crop top—and couldn't believe any guy could be that stupid.

This woman was made to be fucked, worshipped, bred until she couldn't walk. And he walked away?

I lifted her chin gently with my fingers, forcing her eyes to meet mine. "Come here, Autumn. He was a fucking idiot for even thinking that. I'm sure he didn't have the stamina to satisfy a beauty like you anyway."

She blushed hard, cheeks burning even in the cold rain, but she didn't pull away. Instead she stepped closer, her body almost against mine now, soft curves brushing me as another sob hit her.

"I feel like I'm the problem," she whispered, voice cracking. "Like I'm not good enough. And when I saw you with Lily… you both looked so happy. I felt like Lily was better, like she was enough for you… even though her husband's still with her."

Her words hung heavy in the storm, raw and vulnerable.

I pulled her the rest of the way in, arms wrapping around her tight, her soaked tits pressing soft and warm against my chest.

"You're more than enough," I murmured against her wet hair. "Way more. And right now, you're with me."

She clung harder, body trembling—not just from the cold.

The rain poured down, washing everything clean.

And I wasn't letting her go.

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